US4230866A - Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof - Google Patents
Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof Download PDFInfo
- Publication number
- US4230866A US4230866A US06/039,935 US3993579A US4230866A US 4230866 A US4230866 A US 4230866A US 3993579 A US3993579 A US 3993579A US 4230866 A US4230866 A US 4230866A
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- US
- United States
- Prior art keywords
- process according
- aryl
- isoxazol
- base
- benzoic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Definitions
- This invention relates to the preparation of isoxazol5-yl benzoic acid salts that are useful in agriculture.
- salts prepared in accordance with the present invention are salts of free acids which have the following structure. ##STR1##
- a salt of 3-aryl-isoxazol-5-yl benzoic acid is prepared by base treatment of 3'-(aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one.
- 3-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones have been disclosed in our co-pending application Ser. No. 971,462, filed Dec. 20, 1978, which is herewith incorporated by reference, and are prepared as disclosed therein by reaction of a nitrile oxide with 3-methylenephthalide in accordance with the following equation: ##STR2##
- Aryl radical takes no appreciable part in the reaction, any aromatic radical or heteroaromatic radical, e.g., pyridyl, may be used.
- Aryl is a radical of the following formula ##STR3## wherein X and Y are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, halo-lower-alkyl, phenoxy, phenyl and cyano.
- lower alkyl and “lower alkoxy” are understood to include those alkyl and alkoxy groups having up to five carbon atoms, inclusive. Both straight as well as branched chain alkyl groups are contemplated.
- halo-lower-alkyl as used herein is understood to mean those lower alkyl groups in which at least one, and perhaps all, of the hydrogen atoms have been replaced by halogen atoms. It is to be clearly understood that trifluoromethyl is contemplated as being a halo-lower-alkyl moiety.
- halogen as used herein includes chlorine, bromine, fluorine and iodine.
- the spiro compound is mixed with a strong base resulting in a salt of 3-aryl-isoxazol-5-yl benzoic acid.
- a stoichiometric amount of base may be utilized it is preferable to dissolve the base in water and utilize a slight excess. Additional solvents have been found to enhance the reaction.
- the reaction may be conducted at room temperature and atmospheric pressure. Although temperatures and pressures above ambient may be utilized, for obvious reasons ambient conditions are preferred.
- the specific base used is not critical. However, the use of strong bases increases the rate of reaction. Generally, the base used should be of sufficient basicity to abstract the hydrogen from the 4-position of the isoxazoline ring. It is thought that a base having a pK A of 11 or more will be sufficient. This includes but is not limited to such bases as alkali metal hydroxides, alkaline earth hydroxides, alkali metal carbonates, aliphatic amines, etc.
- the salt may be converted to the free acid by acidification. Additionally, the acid may be converted to an ester utilizing known procedures.
- a solvent is utilized the specific solvent used is not critical. It is desirable, however, to utilize a water-miscible solvent in order to enhance the reaction of the spiro compound with the base. This is especially true if an aqueous base is a reactant.
- Useful solvents include water, alcohol, dioxane, tetrahydrofuran, dimethylsulfide and the like.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
3-Aryl-isoxazol-5-yl benzoic acid and salts thereof are prepared by base treatment of 3'-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one.
Description
This invention relates to the preparation of isoxazol5-yl benzoic acid salts that are useful in agriculture. Specifically, salts prepared in accordance with the present invention are salts of free acids which have the following structure. ##STR1##
Belgian Pat. No. 837,454 discloses such compounds to be effective plant growth regulants. In addition, U.S. patent application Ser. No. 796,248, filed May 12, 1977, now abandoned, U.S. patent application Ser. No. 907,069, filed May 18, 1978, now abandoned, and U.S. patent application Ser. No. 966,403, filed Dec. 4, 1978, all of which are herewith incorporated by reference, disclose that such compounds are useful in regulating the growth of desirable plants as well as controlling the growth of undesirable plants. Said applications disclose that the isoxazol-5-yl benzoates are prepared by conversion of isoxazolin-5-yl benzoate with N-bromosuccinimide or dichlorodicyanobenzoquinone. Isoxazolin-5yl benzoates are prepared, however, from vinyl benzoates which are somewhat difficult to prepare.
In accordance with the novel aspects of the present invention, a salt of 3-aryl-isoxazol-5-yl benzoic acid is prepared by base treatment of 3'-(aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one. 3-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones have been disclosed in our co-pending application Ser. No. 971,462, filed Dec. 20, 1978, which is herewith incorporated by reference, and are prepared as disclosed therein by reaction of a nitrile oxide with 3-methylenephthalide in accordance with the following equation: ##STR2##
Since the Aryl radical takes no appreciable part in the reaction, any aromatic radical or heteroaromatic radical, e.g., pyridyl, may be used. Preferably, however, Aryl is a radical of the following formula ##STR3## wherein X and Y are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, halo-lower-alkyl, phenoxy, phenyl and cyano.
As used herein, the terms "lower alkyl" and "lower alkoxy" are understood to include those alkyl and alkoxy groups having up to five carbon atoms, inclusive. Both straight as well as branched chain alkyl groups are contemplated.
The term "halo-lower-alkyl" as used herein is understood to mean those lower alkyl groups in which at least one, and perhaps all, of the hydrogen atoms have been replaced by halogen atoms. It is to be clearly understood that trifluoromethyl is contemplated as being a halo-lower-alkyl moiety.
The term "halogen" as used herein includes chlorine, bromine, fluorine and iodine.
In accordance with the process of the invention, the spiro compound is mixed with a strong base resulting in a salt of 3-aryl-isoxazol-5-yl benzoic acid. Although a stoichiometric amount of base may be utilized it is preferable to dissolve the base in water and utilize a slight excess. Additional solvents have been found to enhance the reaction.
The reaction may be conducted at room temperature and atmospheric pressure. Although temperatures and pressures above ambient may be utilized, for obvious reasons ambient conditions are preferred.
The specific base used is not critical. However, the use of strong bases increases the rate of reaction. Generally, the base used should be of sufficient basicity to abstract the hydrogen from the 4-position of the isoxazoline ring. It is thought that a base having a pKA of 11 or more will be sufficient. This includes but is not limited to such bases as alkali metal hydroxides, alkaline earth hydroxides, alkali metal carbonates, aliphatic amines, etc.
If desired, the salt may be converted to the free acid by acidification. Additionally, the acid may be converted to an ester utilizing known procedures.
If a solvent is utilized the specific solvent used is not critical. It is desirable, however, to utilize a water-miscible solvent in order to enhance the reaction of the spiro compound with the base. This is especially true if an aqueous base is a reactant. Useful solvents include water, alcohol, dioxane, tetrahydrofuran, dimethylsulfide and the like.
In order to illustrate the novel aspects of the present invention, the following examples are presented. Said examples are presented for illustration and are not intended as a limitation with respect to the scope of the invention.
To 3'-(o-methylphenyl)-spiro[isobenzofuran-1 (3H),5'(4'H)-isoxazol]-3-one (2.5 g, 0.0085 mole) in 25 ml of ethanol was added a solution 0.6 g (0.015 mole) of sodium hydroxide in 25 ml of water. The solution was stirred for two hours. An additional 50 ml of water was added and stirring continued resulting in a solution containing a salt of the desired acid. The solution was then acidified with concentrated hydrochloric acid and extracted with 200 ml of ether. The ethereal solution was washed two times with water, dried over calcium sulfate and concentrated under a vacuum to give 2.40 g of the desired acid as white crystals, mp. 158.5°-159.5° C. The crystals were recrystallized from 10 ml of acetonitrile to give 1.55 g of colorless crystals, mp 160.5°-161.5° C.
Anal. Calc'd: C,73.11; H,4.69. Found: C,73.08; H,4.71.
To 1.0 g of 3'-(m-trifluoromethylphenyl)-spiro [isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one dissolved in 25 ml of ethanol was added 20 ml of a 1 N sodium hydroxide solution. The solution was stirred at room temperature for five hours giving the sodium salt of the desired acid. The clear solution was acidified with concentrated hydrochloric acid, extracted with 300 ml of ether, washed two times with water, dried over calcium sulfate and concentrated to give 0.98 g of the desired acid as a white solid, mp 175°-176° C.
Utilizing the procedure of Example 1, 2-[3-(m-cyanophenyl)-5-isoxazolyl]benzoic acid, mp 195°-196° C., was prepared.
Anal. Calc'd: C,70.34; H,3.47. Found: C,70.22; H,3.49.
The above examples disclose an efficient process for preparing 3-aryl-isoxazol-5-yl benzoic acids and salts thereof that are useful as herbicides and plant growth regulants. If desired, the acid may be esterified resulting in additional herbicides and plant growth regulants.
Although this invention has been described with respect to specific modifications, the details thereof are not to be construed as limitations, for it will be apparent that various equivalents, changes and modifications may be resorted to without departing from the spirit and scope thereof and it is understood that such equivalent embodiments are intended to be included herein.
Claims (9)
1. A process for preparing a salt of 3-Aryl-isoxazol-5-yl-benzoic acid which comprises reacting a spiro compound having the formula ##STR4## with a base having a pKA of 11 or more, in the presence of a water-miscible solvent.
2. A process according to claim 1 wherein said base is selected from the group consisting of alkali metal hydroxides, alkaline earth carbonates, alkali metal carbonates and aliphatic amines.
3. A process according to claim 1 wherein said Aryl is ##STR5## wherein X and Y are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, halo-lower alkyl, phenoxy, phenyl and cyano.
4. A process according to claim 3 wherein X is hydrogen and Y is halo-lower alkyl.
5. A process according to claim 4 wherein said spiro compound has the formula ##STR6##
6. A process according to claim 5 wherein said trifluoromethyl moiety is in the meta position.
7. A process according to claim 6 wherein said base is an alkali metal hydroxide.
8. A process according to claim 7 which comprises reacting a spiro compound having the formula ##STR7## with sodium hydroxide in the presence of an alcohol.
9. A process according to claim 1 further comprising the step of reacting the salt produced by the process of claim 1 with an acid to form the free acid of said salt.
Priority Applications (34)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/039,935 US4230866A (en) | 1979-05-17 | 1979-05-17 | Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof |
ES488768A ES488768A0 (en) | 1979-02-22 | 1980-02-20 | A PROCEDURE FOR PREPARING ACID 2- (3-ARIL-5-ISOXAZOLIL) -BENZOIC |
DE8080300481T DE3065860D1 (en) | 1979-02-22 | 1980-02-20 | Thermolysis of 2-(3-aryl-isoxazol-5-yl)benzoic acids, salts and halides from 3'-(aryl)-spiro(isobenzofuran-1(3h),5'(4'h)isoxazol)-3-ones |
EP80300481A EP0015140B1 (en) | 1979-02-22 | 1980-02-20 | Thermolysis of 2-(3-aryl-isoxazol-5-yl)benzoic acids, salts and halides from 3'-(aryl)-spiro(isobenzofuran-1(3h),5'(4'h)isoxazol)-3-ones |
AT80300481T ATE5587T1 (en) | 1979-02-22 | 1980-02-20 | THERMOLYTIC PROCESS FOR THE PREPARATION OF 2-(3-ARYLISOXAZOLE-5-YL)BENZOACIDS, THEIR SALTS AND HALOGENIDES FROM 3'-(ARYL)-SPIRO(ISOBENZOFURAN-1(3H),5'(4'H)ISOX ZOL)- 3-ONES. |
MX808653U MX5929E (en) | 1979-02-22 | 1980-02-21 | PROCEDURE FOR PREPARING ACID DERIVATIVES 2- (3-ARIL-5-ISOXAZOLIL) -BENZOIC |
BG8048155A BG31500A3 (en) | 1979-02-22 | 1980-02-21 | Method for obtaining of 2/3- arjl- 5- isoxazol/ benzoilhalid |
DK75180A DK75180A (en) | 1979-02-22 | 1980-02-21 | METHOD FOR PREPARING 2- (3-ARYL-5-ISOXAZOLYL) -BENZOIC ACIDS OR SALTS OR HALOGENIDES THEREOF |
BG8046704A BG30928A3 (en) | 1979-02-22 | 1980-02-21 | Method for obtaining of 2- /3- aryl- 5- isoxazolin benzoic acids |
CA000346196A CA1137493A (en) | 1979-02-22 | 1980-02-21 | Thermolysis of 2-(3-aryl-isoxazol-5-yl) benzoic acids, salts and halides from 3'-(aryl) -spiro [isobenzofuran-1(3h), 5'(4'h)isoxazol] -3-ones |
TR20875A TR20875A (en) | 1979-02-22 | 1980-02-21 | THERMOLYM OF 2- (3 ARIL-IZOXAZOL-5-IL) BENZOIC ACIDS, SALTS AND HALOGENUERS FROM 3- (ARIL) -SPIRO / IZOBENZOFURAN-1 (3H, 5 '(4'H) ISOXAZOL / -3'ONS |
BG8048156A BG31501A3 (en) | 1979-02-22 | 1980-02-21 | Method for obtaining of 3- arjl- isoxazol- 5- il- benzene carbonic acid and its salts |
YU00470/80A YU47080A (en) | 1979-02-22 | 1980-02-21 | Process for obtainin 2-(3-aryl-5-isoxazolyl-benzoic acid |
AR280040A AR222067A1 (en) | 1979-02-22 | 1980-02-21 | PROCEDURE FOR PREPARING ACID 2- (3-ARIL-5-ISOXALIL) -BENZOIC, AND ITS SALTS |
BR8001036A BR8001036A (en) | 1979-02-22 | 1980-02-21 | PROCESS FOR THE PREPARATION OF 2- (3-ARYL-5-ISOXAZOLIL) -BENZOIC ACID, FOR THE PREPARATION OF A 3-ARYL-ISOXAZOL-5-IL-BENZOIC ACID SALT, AND FOR THE PREPARATION OF A HALOGENIDE OF 2- (3-ARIL-5-ISOXAZOL) -BENZOYL |
HU80403A HU184724B (en) | 1979-02-22 | 1980-02-21 | Process for producing 2-bracket-3-phenyl-isoxazol-5-yl-bracket closed aenzoic acid derivatives and salts and halogenides from 3-comma above-phenyl-spiro-square bracket-isobenzofurane-1-bracket-3h-bracket closed,5-comma aaove-bracket-4-comma above-h-bracket closed-isoxazol-square bracket closed-3-one derivatives |
PH23670A PH14889A (en) | 1979-02-22 | 1980-02-21 | Thermolysis of 2-(3-aryl-isoxazol-5-yl)benzoic acids,salts and halides from-(aryl)-spiro(isobenzofuran-1(3h),5'(4'h)-isoxazol)-3-ones |
RO100262A RO80464B (en) | 1979-02-22 | 1980-02-21 | Process for preparing some 2-(3-aryl-5-il) benzoic acid derivatives |
DD80219203A DD151062A5 (en) | 1979-02-22 | 1980-02-21 | PROCESS FOR THE PREPARATION OF 2- (3-ARYL-5-ISOXAZOLYL) Benzenesäure |
NO800486A NO150278C (en) | 1979-02-22 | 1980-02-21 | PROCEDURE FOR THE PREPARATION OF 2- (3-ARYL-ISOXAZOL-5-YL) -Benzoic Acid Compounds |
CS819141A CS221966B2 (en) | 1979-05-17 | 1980-02-21 | Method of preparation of the 2-/aryl-5-isoxazolyl/benzoyl halogenide |
AU55790/80A AU527290B2 (en) | 1979-02-22 | 1980-02-21 | Preparation of isoxazolyl benzoic acids |
RO109857A RO85817B (en) | 1979-02-22 | 1980-02-21 | Process for preparing 2-(3-aryl-isoxazol-5-yl)-benzoic acid halides |
IL68554A IL68554A (en) | 1979-02-22 | 1980-02-22 | Process for the preparation of 2-(3-aryl-5-isoxazolyl)benzoyl halides |
IL59451A IL59451A0 (en) | 1979-02-22 | 1980-02-22 | Thermolysis of 2-(3-aryl-isoxazol-5-yl)benzoic acids,salts and halides from 3'-(aryl)-spiro(isobenzofuran-1(3h),5'(4'h)isoxazol)-3-ones |
ES491274A ES8104260A1 (en) | 1979-02-22 | 1980-05-08 | Thermolysis of 2-(3-aryl-isoxazol-5-yl)benzoic acids, salts and halides from 3'-(aryl)-spiro(isobenzofuran-1(3H),5'(4'H)isoxazol)-3-ones. |
ES491273A ES491273A0 (en) | 1979-02-22 | 1980-05-08 | A PROCEDURE FOR PREPARING A 3-ARYL-ISO-XAZOL-5-ILBENZOIC ACID SALT |
PH25909A PH17486A (en) | 1979-02-22 | 1981-07-14 | Preparation of 3-aryl-isoxazoles-5-yl-benzoic acid and salt thereof |
CA000400328A CA1137494A (en) | 1979-02-22 | 1982-03-31 | Thermolysis of 2-(3-aryl-isoxazol-5-yl) benzoic halides from 3'-(aryl)-spiro[isobenzofuran-1(3h), 5'(4'h)isoxazol]-3-ones |
IN1177/CAL/82A IN155200B (en) | 1979-02-22 | 1982-10-12 | |
NO831258A NO151006C (en) | 1979-02-22 | 1983-04-08 | PROCEDURE FOR PREPARING 2- (3-PHENYL-ISOXAZOL-5-YL) -BENZOYL HALOGENIDES |
NO831257A NO831257L (en) | 1979-02-22 | 1983-04-08 | PREPARATION OF SALTS OF 2- (3-ARYL-ISOXAZOL-5-YL) -BENZO ACIDS |
IL68554A IL68554A0 (en) | 1979-02-22 | 1983-05-03 | Process for the preparation of 2-(3-aryl-5-isoxazol)benzoyl halides |
IN1178/CAL/82A IN155201B (en) | 1979-02-22 | 1985-02-21 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/039,935 US4230866A (en) | 1979-05-17 | 1979-05-17 | Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
US4230866A true US4230866A (en) | 1980-10-28 |
Family
ID=21908162
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/039,935 Expired - Lifetime US4230866A (en) | 1979-02-22 | 1979-05-17 | Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof |
Country Status (2)
Country | Link |
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US (1) | US4230866A (en) |
CS (1) | CS221966B2 (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3947263A (en) * | 1974-07-29 | 1976-03-30 | Uniroyal, Inc. | Plant growth regulants |
US3964896A (en) * | 1971-08-09 | 1976-06-22 | Uniroyal, Inc. | Oxadiazole benzoic acid derivatives as herbicides |
US4032644A (en) * | 1975-12-29 | 1977-06-28 | Sandoz, Inc. | Isoxazolyl benzoic acids |
GB1494877A (en) * | 1975-01-10 | 1977-12-14 | Commw Scient Ind Res Org | Heterocyclic compounds and plant growth regulating compositions |
US4135910A (en) * | 1977-05-12 | 1979-01-23 | Monsanto Company | Oxadiazol-3-yl-benzoates as plant growth regulants |
US4140515A (en) * | 1977-05-12 | 1979-02-20 | Monsanto Company | Aryl-3-isoxazole benzoates as plant growth regulants and herbicides |
-
1979
- 1979-05-17 US US06/039,935 patent/US4230866A/en not_active Expired - Lifetime
-
1980
- 1980-02-21 CS CS819141A patent/CS221966B2/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3964896A (en) * | 1971-08-09 | 1976-06-22 | Uniroyal, Inc. | Oxadiazole benzoic acid derivatives as herbicides |
US3947263A (en) * | 1974-07-29 | 1976-03-30 | Uniroyal, Inc. | Plant growth regulants |
GB1494877A (en) * | 1975-01-10 | 1977-12-14 | Commw Scient Ind Res Org | Heterocyclic compounds and plant growth regulating compositions |
US4032644A (en) * | 1975-12-29 | 1977-06-28 | Sandoz, Inc. | Isoxazolyl benzoic acids |
US4135910A (en) * | 1977-05-12 | 1979-01-23 | Monsanto Company | Oxadiazol-3-yl-benzoates as plant growth regulants |
US4140515A (en) * | 1977-05-12 | 1979-02-20 | Monsanto Company | Aryl-3-isoxazole benzoates as plant growth regulants and herbicides |
Also Published As
Publication number | Publication date |
---|---|
CS221966B2 (en) | 1983-04-29 |
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